Romeo MILF Pleaser
by snakebit1995
Summary: Romeo is an attractive young man living in a upper class neighborhood, and the local older women have started to take notice. Contains- LEMONS, MILFs
1. Chapter 1: Lucy

_Italics indicate thinking_

 **People seemed interested in this idea, so enjoy.**

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 **NO POV**

I a quiet little suburban town, the upper-class neighborhood was sparking back to life, mini mansions and estates waking up for a new day was beginning, Lucy Heartfilia was one of these people waking up, she put on her robe and got ready for the day. Lucy was the trophy wife of Natsu, an important business man. Trophy wife sounded rude because they were in love, she was more of a trophy wife in spirits, forty-seven, blonde, big breasts, rich lifestyle, didn't have to work…it was actually sounding worse the more she thought about it.

They had lived in this new neighborhood for a few years, her husband and their daughter Wendy. Wendy had been somewhat unfortunate, she hadn't inherited Lucy's well endowed natural figure but she didn't seem to mind all that much.

"Alright Mom I'm going to hang out with Shelia." The girl skipped rapidly down the stairs.

"Enjoying the last few days of summer before senior year?" Lucy smiled.

"Something like that." Wendy grabbed the keys to her car and headed out, and since Natsu was on a business trip their mini mansion was empty except for the older mature blonde.

Lucy sighed a bit and sat around in her nightgown and robe, she didn't even feel like bothering to get dressed right now.

Despite pushing Fifty Lucy was still considered gorgeous, she had large natural breasts, although recently they started sagging a bit, long blonde hair with a few grey hairs that she dyed out, and the slightest hint of wrinkles covered by makeup, and with her daughter in highschool most people agreed she was a MILF by the strict definition.

"Maybe I'll go out to the pool." She thought going upstairs.

She liked the sound of spending a day by the pool, sipping iced tea, sun bathing and all that. She threw on a cute yellow bikini that hugged her mature body and made herself a drink, after all that was ready she went out by her pool and laid out on her lounger.

It seemed no one else in the neighborhood was out right now, it was quiet, she couldn't hear her neighbors but that wasn't unexpected, to her right was the Conbolt house, living there was a son and single father. The father was out almost all the time Lucy rarely if ever saw him, the son Romeo though was friends with her daughter, they were in the same class in high school. He was a handsome kid Lucy wished Wendy would make a move on the kid.

"Hmm." Lucy sipped from a class with iced tea in it as she heard a nearby sliding door push open.

She turned her head, sunglasses blocking any glare as she saw the boy she was just talking about walking out to his own pool.

"Oh…wow." Lucy gulped.

He was just wearing a speedo one with quite the bulge in it and he was quite toned. When did he start looking so, good, how had she never seen how much of a little stud was living right next door. She partially felt bad about thinking these things since she was married but…damn.

"Oh good morning Miss Dragneel." The boy waved at her from across the fence.

"Hello." Lucy looked him over "Out for a swim?"

"Yeah trying to get a few more in before the end of the summer." He stretched, his abs crunching and his biceps popping with strenght a bit.

" _Oh you gotta be kidding me."_ Lucy nearly drooled _"And that bulge? How's a kid his age packing something like that?"_

Lucy watched her daughter's friend swim around for a while, muscles glistening with water and sweat, soon though it was noon and the hot august sun was baking down on them.

"Romeo?" Lucy walked over to the stomach high fence that separated their property and leaned her breasts on it "Why don't you come over, I'll make some lunch."

"Really, sure." He smiled.

Lucy went inside around the house and opened the door for the boy only to see he put on a shirt, she was rather disappointed that he covered up his toned teen body but she was still able to get a good peak at his undercarriage which was the main dish of her eye candy.

She made some sandwiches and sat and chatted with him, making sure to tease him a bit, leaning her large chest on the counter, never bothering to cover her bikini clad body any more than she already had. She teased him a bit about Wendy, trying to get the two of them together.

"I know she might not have my figure but Wendy is a catch." Lucy told him "Don't let her pass you by."

"Yes Miss Dragneel." Romeo mostly dismissed her.

"But hey like they say take a look at her mother and you'll see what a girl will look like when she's older." Lucy smiled "Maybe she's got a growth spurt coming on."

"Well that wouldn't be terrible." Romeo blushed a bit.

"Oh why, you think an old woman like me looks good?" Lucy teased him some more.

"You're not old." Romeo told her "And you look great."

"Wow thanks, if I was thirty years younger I'd snatch you up myself you little charmer." Lucy said.

"Good to know." Romeo laughed a bit.

Lucy walked over towards him "Unless you…like older women?"

"Miss Dragneel?" Romeo was clearly nervous as the MILF got close to him.

"Please…call me Lucy." She smiled with a sultry look before suddenly kissing him.

"HMM!" Romeo kissed back and held her hips, his hands reaching back to touch her ass/

"Come on you little stud." Romeo was clearly shocked but not turned off by the sudden escalation by the older woman taking his hand and leading him upstairs to her room.

Once up there she quickly pulled his shirt off to see his hard abs.

"Someone's been working out." She hummed tugging at his swimsuit.

"Yeah." Romeo laughed "I do a lot of stuff to stay in shape."

"I'm not complaining." Lucy pulled his speedo down "Oh my, how big."

"HMM!" Romeo let out a small gasp as Lucy started stroking him "Should we really be doing this?"

"Don't be so nervous." Lucy licked the tip of his cock "You're no virgin I'm sure, but have some fun with a real woman, MMMM!"

Lucy started sucking and bobbing her head, breaking down any last bit of Romeo that was going to hold back from her.

"Hmm, you've got a good one." Lucy licked the shaft while stroking it.

Romeo moaned holding Lucy's head a bit as she bobbed back and forth and sucked him off, his long thick shaft getting coated in her saliva, his lime sized balls quivering a bit with each of her suction heavy gurgles.

"Enough foreplay." Lucy kneeled up on the bed and started taking her bikini off "Lets get to the good part."

Romeo used his hands to explore Lucy's mature body, rubbing her breasts, pulling down her bikini bottoms to grab her ass, Lucy was giggling and moaning as she was played with by the schoolboy. Eventually she was laying on her back on the bed, legs spread and rubbing her pussy as Romeo stroked his cock to keep it at full mast.

"Come here." Lucy licked her lips as Romeo got close.

"HMM UIGH!" Romeo groaned pushing into her.

"OHHH!" Lucy moaned as she felt the thick cock push into her.

Romeo held her hips and started thrusting as Lucy rocked against him a bit, her breasts swaying around on her chest as she let out womanly moans to compliment his more boyish grunts.

"OH HARDER!" Lucy moaned "LIKE YOU MEAN IT!"

"I'm-UGH!" Romeo grunted as the MILF's pussy took him deeper and deeper.

"You're not seriously cumming already are you?" Lucy laughed "How weak."

"GRRR!" Romeo thrusted more and more, groaning back as he fucked Lucy, his balls slapping on her thighs for satisfying clapping and fapping noises while his cock plunged into her perfectly "AHHH!"

Lucy felt him release inside her, she would have preferred a little more but she also took some pride in having made him cum so quickly.

"Don't relax just yet you little stud." Lucy smirked.

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **So people were kinda interested in Romeo having sex with Fairy Tail MILFs, so here it is, the first is just a short intro about him and his first time with an older woman. I plan to have more unique interactions and have him take more charge later.**

 **Suggest what you want to see in the future.**

 **Till Next Time!**


	2. Chapter 2: Juvia

_Italics indicate thinking_

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 **NO POV**

Today was the annual end of summer block party for the Hills section of town. There were plenty of people chatting, playing lawn games and doing even more.

"Hello Juvia." Lucy sat at the table with one of her fellow housewives and handed her a glass of wine "What's got you looking so drab?"

"I've been feeling lonely as of late." The woman said.

Juvia was another attractive MILF trophy wife living in the Hills.

"I just had a baby but…it feels like Gray doesn't like me as much, perhaps my body has degraded." The woman sighed fixing her sun dress.

"I think you look great." Lucy laughed "So you two just aren't doing it?"

"Yes." Juvia frowned.

"Maybe you need someone else to…reignite your sexiness." Lucy smiled.

Juvia sighed "Who would even want to have sex with Juvia anyway."

"Well…I know a hot young stud who's pants you might be able to flirt into, I was able to after all." The blonde smirked and looked at Romeo who was chatting with some of the kids in his age group.

"You didn't!" Juvia gasped.

"I did." Lucy blushed "And…it was amazing, he was like a stallion."

"Hmm." Juvia blushed "Well."

"Seriously, think about it." Lucy got up.

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 **Later**

It has been a few days since the block party and Juvia had been thinking about what Lucy said for a while…and she was gonna do it. This attractive 43 year old was gonna have sex with someone more than half her age, just thinking about it was a bit exhilarating.

She had known Romeo for a few years, he lived a few blocks over and since everyone around here was so friendly he didn't think much of it when she asked him over to clean her garage for a few bucks.

"Where's your husband today?" Romeo asked Juvia.

"He took the baby to visit his mother, he'll be back tomorrow." Juvia said "Until then Juvia has a day to herself to relax."

Juvia was standing around in a tight t-shirt and jean shorts while Romeo was in a loose tank top and basketball shorts.

"Thank you so much for helping me with this Romeo." Juvia smiled "You can shower off upstairs real quick and then I'll get your money."

"Sure, if you don't mind." He said.

"Not at all." Juvia sent him upstairs.

She waited downstairs for a bit until the water came on, the hissing of the shower audible from downstairs.

"Okay…no going back." She nodded and headed upstairs.

Juvia got close to her bathroom which was connected to her master and peeked in.

"Wow." She gasped under her breath seeing the steamy sight of the hot young man in her shower.

The water running down his hard abs and pecs, his long thick shaft dangling around between his legs as he washed up, his balls sagging down.

Juvia knew it was now or never, she took a deep breath and stripped down to nothing, her pale skin on display as she stepped out, put a hand on her hips and ruffled her hair while making a sexy face.

"Oh Romeo~" she cooed.

"huh-WA!" the boy saw her and quickly covered himself "Miss Fullbuster!"

"I seem to have misplaced my purse." She walked towards the hot shower "Perhaps I can pay you…another way."

She stepped into the shower and pressed her body against him as the water rushed down her back.

"The ladies around the neighborhood have had their eye on you for a while." Juvia reached down and slowly stroked his shaft "I'm glad to know the high expectations paid off, you've become a handsome young man."

"Miss Fullbuster." Romeo groaned with pleasure, his hands finding their way to her waist and thick thighs as she stroked him.

"Nuh-uh." She smirked "Just call me Juvia sweetie."

"MMM!" Romeo groaned as she stroked him more and more while her body was soaked with the hot steam and water of the shower "That's so good."

"It's good to know those hands of yours are good for more than just moving boxes." Juvia moaned as he squeezed her ass "OHHH!"

Juvia moaned as Romeo reached back and slipped a couple fingers into her loose pussy, making her gasp from the pleasure as her pumped her with his digits while she pumped his cock in return.

The two kept on grinding together while Rubbing their hands over the others crotch. After she had been finger fucked to the point of near orgasm Juvia squatted down and took Romeo into her mouth, the water of the shower still running and wetting her hair.

"MMM GURK!" she coughed a bit as the meaty shaft pushed down her throat.

"Ohh yeah that's good." Romeo moaned as he leaned on the wall of the shower and Juvia sucked him off.

Juvia made sure to tease him with loud sucking sounds before swirling her tongue a bit and making him get excited.

"UGH!" Romeo started cumming without warning, filling her mouth with his hot and sticky seed.

"So much~" Juvia moaned as jizz leaked down her tongue "You're not gonna make me settle for just that are you?"

"Not at all." Romeo smirked as she backed her ass up against him and leaned on the wall.

"OHHH!" Juvia let out a wonderful moan as Romeo pushed into her and started thrusting.

She was rocked back and forth with each pump of his hips, her breasts would sag and slap around while her ass collided with his crotch, her plump rear jiggling softly.

"FUCK!" Juvia moaned "Ohh harder! Harder please!"

Romeo grunted and started to up his thrusting speed, his long hard shaft plunging deeper and deeper while his balls slapped against her thighs, her water made the sex a bit rougher but neither complained about it.

"Yes, yes I'm so close!" Juvia moaned "I'm going to…OHHH!"

He loose snatch flexed around his rod and milked him dry as Romeo groaned and started cumming in her, filling her pussy with his spunk.

"Hmm, that was wonderful I missed feeling like that." Juvia hummed.

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **Suggest ideas for the future**

 **Till Next Time!**


	3. Chapter 3: Erza

_Italics indicate thinking_

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 **NO POV**

Summer was officially over which meant school was back in session…and even though it wasn't even a full week in Romeo was already in detention.

What could possibly get someone into trouble on the first day of school, stupid senior pranks that's what. Since he was a senior Romeo had been convinced by his friends to pull said prank…running down the hall naked. It didn't take long to get him in trouble and now he was staying after to sit in a room and do nothing for a few hours.

Watching him today was one of the strictest teachers in the whole school, Miss Scarlet. Erza Scarlet was a 50-year-old teacher, most students feared her since she was ruthless with her detentions and was willing to punish for the slightest offense. Most people also found her a bit bitter, probably cause in her older age she was still single even with her looks. She had long red hair with some hints of greying that she tried to dye out, at school she was usually wearing a suit like outfit, a tight blouse over her large bust, a skirt and stockings on her long legs and sizable rear.

"Hmm." She sat as her desk and adjusted her glasses while watching Romeo sit quietly at his desk "Already starting off on a bad year Mr. Conbolt."

"Whatever." He mumbled.

"What could possibly posses you to think that such a thing is acceptable." Erza sighed.

"It was just a joke." He shrugged "People thought it was funny, and girls like it."

Erza blushed a bit at this, she had witnessed the incident in question and got quite the look at Romeo…and it was hard to get out of her head, even if she thought thinking that way about a student was wrong.

"I don't see what the big deal is." Romeo shrugged.

"The big deal is that it's uncouth to do such a thing, running around with your penis flopping about." Erza huffed.

"I bet you liked it, probably the first one you've seen this century." Romeo mumbled under his breath.

"What was that?" Erza glared passed her glasses.

She stood up and walked towards him, her heels clicking on the floor with each step she took, she got close to his desk and slammed her hands down.

"Take them off." She said.

"What?" Romeo gasped.

"Your pants, take them off." Erza demanded.

Romeo wasn't sure what was happening but Erza clearly wasn't fooling around, he stood up and started to undo the button on his shorts.

"So you think I don't know how to handle a cock huh?" she grabbed his shaft.

"Whoa!" he gasped.

Erza rubbed her hand up and down on his shaft to pleasure him while smirking a bit "I know how boys like you are, always thinking stupidly I'll have to discipline you."

Erza squatted down and started licking his shaft, slowly taking his cock into her mouth. Romeo couldn't believe it was happening but it felt so good it was definitely real, where had this side of this teacher been all this time.

"HMM!" Erza moaned bobbing her head slowly to suck him off.

Her tongue twirled and her lips glided over his twitching shaft, Romeo getting more and more turned on by her moans. Erza of course smirked with a hint of pride, all those students thinking she was some lonely old hag would never believe she was on her knees giving a student a blowjob, she could barely believe it herself.

"UGH!" Romeo groaned blowing a load on her face, his hot cum dripping onto her glasses.

"That was really the best you could do?" Erza took her glasses off and smirked.

"No, I've got more." Romeo stood her up and rubbed her ass a bit as she started cleaning off her desk to make room.

Erza locked the door and started taking her top off, stripping down and standing before Romeo nude save for her leggings which were clipped to her panties. Erza was fifty and unfortunately her body had started to show it, her breasts while large had some clear sag and her midsection had gotten a bit pudgy with her age. Romeo was naked as well, his youthful look a stark contrast to her mature body.

Erza laid on the desk and spread her legs, inviting Romeo to prove himself to her.

"Sure, you can handle someone like me, don't want you to hurt yourself Miss Scarlet." He said rubbing his cock on her folds.

"I can handle it-UGH!" she groaned.

Despite her age Erza was still quite tight, she grunted as her walls adjusted to his size, Romeo leaning over her and placing his hands on the sides of her head as he started thrusting.

"OH YES!" Erza moaned as her legs instinctively wrapped around his back, pulling him closer as his hips pumped into her.

Each thrust made Erza's old body shake, her large breasts wobbling around more and more, her soft tummy jiggling just a bit. The pleasure sparking though her nerves made her more and more turned on, her body begging for a release. Erza hadn't had sex in years at this point, and she needed a real release.

"Fuck…fuck…OH FUCK!" she moaned screaming as she came for the first time.

Erza wasn't done yet, mostly cause her partner still hadn't cum, she stood up and leaned on the whiteboard, her big tits pressing against the cold wall, her nipples hardening as a result.

"Incredible." Romeo entered her again "Your pussy is so tight Miss Scarlet."

"I'll take that as a compliment." She hummed as he held her hips while she propped one of her feet up on the runner where you put the markers, demonstrating some shocking flexibility.

The two new lovers moaned together, their bodies grinding against each other as they worked each other to an orgasm, Romeo pushing deep against Erza while her grinded her ass back against him, both getting closer and closer to an orgasm.

"Here it…comes." Romeo groaned "UGH!"

He blasted inside of Erza, the teacher moaning as she finally got that sweet salty white cream.

"Well, I think you've worked off your punishment." Erza smirked "You can go…but don't be shy if you need a private lesson."

"Oh I won't." Romeo smirked stroking his cock.

"I shouldn't have to say anything but…tell anyone and you're dead." Erza smiled

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **Suggest what you want to see in the future.**

 **Till Next Time!**


	4. Chapter 4: Mira

_Italics indicate thinking_

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 **NO POV**

Since he was a senior with a car Romeo needed a way to pay for gas, so he got a job bussing tables at a little restaurant in town. Usually this meant working late on Friday nights to help the owner clean up.

"Thank you so much Romeo." Mirajane, the mature owner smiled as he put some dishes away on a higher shelf.

"It's no big deal." He stepped down.

Mira was an older woman, probably just around 50 or so, her hair was naturally white and her body still looked good for her age with large breasts and shapely birthing hips held under a black pencil skirt.

"There's just a few more dishes and then we can lock up and head home." Mira smiled.

She turned on the water but at the same time the older hose snapped and spayed out some water, soaking her top.

"HA!" she quickly turned off the spray "Figures."

Romeo went over to help but quickly gulped, the tops they wore here were white, so when Mira got soaked he was getting a full see-through view of her bra, a lacy black and cream-colored garment.

"Ugh." Mira started unbuttoning her top "Sorry about that."

"Umm…" Romeo gasped.

"Oh you don't mind right?" Mira hung her top up and stood there in her bra "I bet a boy like you probably likes this don't ya?"

Romeo blushed more "You're…very pretty."

"Can you tell I used to model." Mira laughed posing "I was pretty popular, your dad's probably heard of me."

"I didn't know you were a model." Romeo said wiping up.

"Oh yeah back in the day…hang on a sec." Mira stepped back into her office and came back out "Look I still have some of the magazines I posed for."

The magazine made Romeo blush, right there on the cover of a sports magazines swimsuit issue was Mira posing in a perfect blue bikini, holding her hair up and making a sensual face for the camera. She looked younger than she did today, this picture was probably almost thirty years old.

"And of course there was this one." Mira giggled opening another magazine to a centerfold where she was laying on silk sheets, surrounded by rose petals…and wearing nothing.

Romeo audibly gulped and tried not to stare.

"This takes me back." Mira smiled "I used to look so good, guys were always sending me letters and stuff."

"You still look great." Romeo said.

"Stop it, you're just being nice." Mira laughed.

"I'm serious, it's taking everything I've got not to just stare at you right now." He explained looking away "I shouldn't…"

"Oh really now…" Mira got a devilish smile on her face as he turned away "Romeo…"

"Yes?" he nervously looked up and his eyes went wide.

Mira reached back and unclipped her bra, letting it drop to the floor as she slid her skirt down "What about now, still able to look away?"

"No Ma'am." He said.

"Hmm." She smirked "Come here."

He walked up and Mira took his hands, placing them on her breasts.

"Well, how do they feel, does this old model still have it?" She asked.

"Hmm, yeah, you do." Romeo played with her soft tits.

"OH…" Mira hummed "I knew hiring you because you were so cute would pay off."

Mira leaned up and started kissing the boy, moaning into his embrace as he played with her tits.

"You seem to know your way around a woman." Mira hummed hopping up on the counter and spreading her legs, pulling her panties to the side to show her wet cunt "How about I give you a meal after work-HAA!"

Romeo leaned in and started dragging his tongue on Mira's pussy, the woman moaning and leaning back on the bar as his tongue slipped deeper into her. Even though she was old Mira still had the body of her younger self, her face had no wrinkles, her breasts no sag, and she was still tight, her walls gripping on to his tongue. Romeo wasn't sure is she was naturally fortunate to look this good at her age, or maybe some of that modeling money went to maintaining this look.

"Yes…hmmm get in there." Mira pushed his head down while teasing her own nipples "Fuck that's good."

Mira held on to the shelf above her for dear life as Romeo wormed his tongue in deeper, her body shaking with pleasure.

"Yes…yes…OHHH YESSS!" she moaned cumming for the first time "HMM!"

Romeo quickly came up and stared kissing her again, rubbing his strong hand on her thigh.

"Oh Romeo!" Mira moaned when he kissed her neck "Hmm, let me see that big cock."

Romeo quickly started getting out of his uniform, standing naked, muscular and hard before her.

"Wow!" Her eyes went wide "I should have made her wear a tighter uniform."

"I'll wear one if you do." Romeo teased her back.

Mira let out a deep mature laugh as she rubbed against him "I'll think about it, just like I've been thinking about giving you a raise."

Romeo rubbed a hand on the inside of her leg. Mira was still sitting on the counter in the kitchen, reaching her legs around she locked herself around him and hugged tight as they kissed, the boy's cock just inches from his boss's warm hole.

"MMMM!" Mira moaned again as she let her ass drop and Romeo entered her.

The two started rocking together, Romeo holding Mira up against the counter as his cock thrusted deeper and deeper, balls slapping against her. Mira rocked her body, her ass occasionally touching the cold counter top as her soft bust pushed against Romeo's hard pecs.

"Yes…oh don't stop." Mira moaned.

The two kept pressing together, both moaning but there was no one around to hear them. Mira's body shivered with pleasure as she drew closer and closer to her climax.

"Hmm…yes…yes…OHH!" Mira screamed as she climaxed.

"UGH!" Romeo blasted inside her.

"Not bad." Mira moaned leaning back "You're a perfect employee."

"Thanks." Romeo smiled.

"Though…I might need you to work late more often." Mira smirked.

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **Suggest what you want to see in the future.**

 **Till Next Time!**


	5. Chapter 5: Shelia

_Italics indicate thinking_

* * *

 **NO POV**

Today Romeo was at the mall with his two friends Wendy and Shelia. Shelia was Wendy's best friend, a girl of equal age with long pink hair that she tied back, a well developed curvy body, and was very popular with boys. Wendy was a little jealous of her friend's body, but never really showed it.

Romeo wasn't planning on going shopping today, but the girls were, and he got dragged along to assist.

"Well how do we look?" Wendy asked stepping out of a dressing room with Shelia, both wearing stripped bikinis, Wendy's blue and green and Shelia's yellow and dark blue.

"Fine." Romeo shrugged "But why are you buying swimsuits since summer is ending now."

"Cause it's the end of season sale so these are super cheap and cute." Shelia smiled as her chest bounced a bit "So we can use them next year."

"If they still fit." Wendy hummed looking at Shelia's bust "I remember a few years ago you brought that strapless one and by March there was no way it would fit."

"I had a growth spurt freshman year." Shelia smiled striking a pose "Don't worry Wendy I'm sure you'll have one soon, just look at your Mom you'll totally grow soon."

"I hope so." Wendy pouted a bit looking at her flat chest.

"Well you two can get changed I'm going to a store myself." Romeo told them.

"You shop alone." Wendy smirked.

"I know how to buy things." the boy rolled his eyes and walked off.

Romeo went across the mall to a men's ware to find what he was looking for, underwear. Unfortunately before he could even look at one item he was tapped on the shoulder.

"So this is what you're buying." Shelia teased.

"HA!" Romeo gasped.

"Seriously." Shelia smirked "Underwear? Did you seriously outgrow the pairs you bought a few months ago?"

"And what if I have?" Romeo asked.

"Then we need to go to the changing room right now." Shelia smirked with a blush.

Despite being best friends with Wendy and knowing she had a bit of a crush on Romeo, Shelia and he had been friends with benefits for a few years now, ever since her aforementioned growth spurt when she caught him checking out her tits. She still remembered their first time at a party, he was a lot smaller then, over the last few months her friend had grown quite the schlong.

"Where's Wendy?" Romeo asked as he and Shelia slipped into a changing room and she quickly got to work getting his pants off.

"Still shopping, I told her I was running to the ATM so we'll need to make this quick." Shelia tugged his pants down and saw his cock spring free "Holy fuck it is bigger!"

"I told you so." Romeo groaned as she started pumping his shaft "My underwear are super tight."

"Seriously how many times do I need to tell you, wear boxers instead of briefs, it'll give you more room." Shelia started licking the tip.

"You wanna try walking around with this thing swinging between your legs?" Romeo rolled his eyes and moaned a bit.

"Never thought about it…sounds kinda hot." Shelia laughed before opening her mouth "HMM!"

She slowly began bobbing her head, softly sucking his cock. Romeo groaned and rubbed the back of his friends head as she sucked him off.

"That's-HHM-weird." Shelia slurped "Normally you moan so much more, where'd you get this resistance from?"

"I don't know, guess I just did." Romeo said not willingly to admit he'd been fucking MILFs the last few weeks.

"Well not like it makes a difference to me." Shelia said getting him good and lubed up "Come on, we need to hurry up."

Shelia wasn't going to bother with any more foreplay, she leaned on the wall and hiked up her skirt, shaking her ass at him, her dark pink panties stretched over her thick backside. Romeo got behind her and slid her underwear down to around her knees and just pushed right into her.

"HMM Fuck~" Shelia moaned bracing her body a bit before reaching up to pull her t-shirt up so she could squeeze her tits.

Romeo's cock pushed and stretched Shelia's walls holding onto her hips and pulling her farther and farther back onto his long thick rod, the pinkette moaning back as her big bust bounced around, smacking into each other softly.

"Oh yes Romeo that's it, just like that." Shelia moaned as her ass smacked into him "Fuck me~"

Romeo was happy to oblige, thrusting his hips more and more to make Shelia's insides quiver and hug his cock back, the two pressing their crotches tighter and tighter together. Romeo leaned over Shelia, reaching around to fondle her tits while his hips kept pumping, his big rod pushing deep, getting ready to flood her full of his hot seed.

"So close…" Shelia moaned as Romeo pinched her nipples "HAAAAA!"

She let out a squeal of pleasure as her pink love canal tightened around Romeo's cock and started milking it for white gold. Romeo grunted and started nutting inside her, semen flooding into the girl.

"Fuck…good job." Shelia moaned fixing her breasts and tucking them back into her bra.

"Well I'll head back to Wendy." Shelia said cleaning herself off and fixing her panties "Meet us at the food court when you're done buying new draws."

"Yeah, yeah." Romeo rolled his eyes.

"You know…you should take Wendy out sometime, I bet she'd be able to handle that bad boy." Shelia smirked.

"I'll think about it." He told her.

"That's what you always say." She sighed walking off.

Even though she was fucking him on the side Shelia was always trying to set her friends up, but Wendy was too nervous and Romeo too dense and noncommittal.

"What took you so long?" Wendy asked when Shelia met back up with her.

"They were restocking the machine so I had to wait." She made up an excuse "Come on let's go eat lunch."

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **Just cause he likes MILFs doesn't mean Romeo can't fuck younger women too.**

 **Suggest what you want to see in the future.**

 **Till Next Time!**


	6. Chapter 6: Ultear

_Italics indicate thinking_

 **Decided to try coming back to this story.**

* * *

 **NO POV**

"OHH AHH!" Juvia moaned loudly as she climaxed.

As Romeo moved off of her he laid next to her on the bed, the housewife pulling the sheets over her body.

"Thank you, Romeo that was wonderful." She smiled "And thanks for your help cleaning out that guest house."

"It was no problem Miss Fullbuster."

"I told you, call me Juvia when we're alone." She said.

"If you don't mind me asking why did you need the guest house cleaned out?" he asked.

"Oh, my sister in law just got a new job here so she's going to be staying with us while she gets settled in." Juvia sighed "I'm afraid you won't be able to come around as much."

"All the more reason to make the time we do have count then." He said reaching over and rubbing her soft pale breasts.

"Romeo." She moaned as he kissed her neck but stopped when they heard a car door "Oh dear it's my husband, quickly get dressed and go, you know the way out the back-window right."

"Yeah." Romeo sighed getting blue balled a bit.

Romeo quickly scampered out the back window on the second floor, sneaking off before Juvia's husband Gray could return. He looked at the guest house, he was curious what the new women moving to the neighborhood would look like.

* * *

 **A couple days later.**

"Thank you for letting me stay with you guys Juvia, I know it was sudden but I couldn't pass up this job." Ultear said.

"It's no trouble." Juvia smiled "I'll be nice to have some extra hands around with the baby."

Ultear Milkovich was Juvia's Sister-In-Law, she was the older sister of Juvia's husband Gray, well half-sister they had different fathers. Juvia was surprised Ultear was changing jobs right now, she was 48 and most people are settled into a job and planning their future retirement in the next ten to fifteen years at that point.

Despite being unmarried Ultear still looked rather attractive with sharp curves, wide hips and full breasts, plus long purple black hair with not a hint of Gray. Juvia was almost jealous…then she remembered Ultear had a doctorate in Physics and could afford all sorts of beauty and spa treatments to keep herself looking rather young and fresh.

"Well, the guest house is all yours." Juvia said with a bit of a smile that showed her annoyance under it, she didn't like her sister-in-law living in her house

"Oh, how kind of you, so accommodating." Ultear said returning the subtle gesture.

Suddenly there was a knock at the door.

"I'll get it." Juvia put her wine glass down and went to open the door "Oh Romeo?"

"Now's not a good time." She leaned in and whispered.

"Who is it?" Ultear asked leaning over.

"Oh, just the boy next door." Juvia said before whispering "You should go."

"Umm some of your mail got delivered to my house by mistake." He handed her a letter "I just wanted to give it to you."

"Oh, well thank you so much." Juvia took it "You're a kind boy."

Romeo left and Juvia closed the door.

"Who was that?" Ultear asked.

"Just Romeo, he lives nearby some of our mail was delivered to him by mistake." Juvia placed the letter down.

"Hmm, he was cute." Ultear chuckled "If all the boys around here look that good, I think I'll like it here, I'm supposed to teach a few classes at the local college too."

"He is quite handsome." Juvia giggled a bit.

"Oh, looking at other men when you have my brother?" Ultear smirked "How naughty."

"N-No it's not like that." Juvia blushed.

"I'm merely teasing." Ultear smiled, her thoughts drifting slightly to the boy.

* * *

 **THE NEXT DAY**

The next day Juvia had to take her baby to a doctor's appointment leaving Ultear alone on the property, the woman walked around the cushy neighborhood trying to get a feel for things.

"Oh, it's that boy from yesterday." She hummed seeing Romeo out for a run.

"Hi." He passed her "Are you new around here?"

"Ultear Milkovich I'm staying with my brother and his wife for a bit." She said.

"I heard about you." He said.

"People have been talking, I've only been here a day." She laughed.

"No Miss Fullbuster had me clean out the guest house and mentioned you were coming to stay there." He said "I just didn't realize it was such a pretty lady."

"Oh, how sly of you." She laughed brushing her sundress "So I have you to thank for having such a nice clean guest house to live in."

"I'm always helping out around the neighborhood." He said "So if you need anything just asked."

"Oh, I can think of a few things you could help me with." She said looking at him.

"What was that?"

"Did I just…say that out loud." She gulped.

Romeo just laughed "It's no big deal."

"Well how about you help me bring the last of my things in from the garage to the guest house." Ultear smiled "I'd really appreciate it they are awfully heavy."

"Sure, that sounds good, they do seem heavy." Romeo looked at her, both subtly hinting at what they thought the other was getting at.

Ultear really did have some bags to be moved and when Romeo got them into her small quaint guest house and put them down.

"Good, there's just two more bags I want you to grab." She said lifting her shirt and flashing her breasts "Fun bags that is."

Romeo reached out and cupped them, the mature woman moaning as he rubbed her gently.

"You certainly are hands on, so strong." Ultear moaned as Romeo stood behind her rubbing her breasts, pulling and pinching her nipples "Hmm, I had a feeling there was more help you gave around this neighborhood than just moving things or mowing lawns."

"I told you I'm always looking to help girls out no matter what it may be." Romeo said as she grinded her soft ass on his crotch.

"I'm no girl." Ultear laughed "I'm a woman."

"I've got plenty of experience with them too." Romeo whispered rubbing her thighs through her jeans.

"I suspected as much." Ultear moaned as they fell back on the bed.

She felt the boy pulling off her clothes and squeezing her soft curves. Ultear had always been a hard worker, but she always enjoyed younger men and frequently would seduce her students in exchange for giving them higher grades. Still even she was surprised by the vigor Romeo displayed, the way he kissed her body, his lips lingering on her soft creamy breasts, the spontaneous fling with the young man made her feel excited and youthful again.

Ultear clung to his hard muscular body as she felt him undressing, his large cock now on display. She smirked and ushered him forward while jiggling her breasts, quickly slapping them around his shaft.

"HMMM!" She started drooling and licking the shaft, lubing it up as she bounced her breasts up and down softly.

"Oh yeah." Romeo moaned as Ultear started sucking his cock while bouncing her breasts around it to stimulate him.

Ultear looked up at him, eyes shadowed with lust as she felt his meaty tip between her lips, the gentle sucking she administered causing little salty drops of his precum to leak out. Romeo was occasionally rolling his hips a bit, pushing more of his cock into her mouth, the feeling of her soft jiggly breasts only making him moan more and more.

Ultear let her breasts fall to the side, she gave Romeo a few more good sucks before flipping over onto her stomach and shaking her ass a bit. Romeo got behind her pressing his hands into her wide sexy ass before spreading her cheeks and pushing his cock into her.

"YES!" Ultear moaned gripping the sheets "Fuck me~"

Romeo started aggressively bucking his hips as he laid on top of her and laid into her, hard cock plunging deep into her tight pussy.

"That's good." Romeo grunted feeling her ass against his abs "You're so hot."

"Just like that!" Ultear screamed feeling his balls slapping her ass.

He leaned into her pushing as deep as he could go as he let out a deep moan and blasted a hot load of cum into her. Of course, Ultear wasn't done and wasted no time pouncing on the boy and keeping him in her room, she had a lot of stress she wanted to work out.

"Hmm?" Juvia arrived home and saw the light was on in the guest house and could hear some rather rancorous coupling going on in there "Jeez, she certainly didn't waste any time."

* * *

 **AN**

 **Thank you for reading. Feedback is appreciated. Feel free to message me any questions or concerns.**

 **Not sure why but I felt like coming back to this.**

 **Suggest girls you'd like to see in the future.**

 **Till Next Time!**


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